Luxury Vacation Home Rentals on Anna Maria Island

Discover our Anna Maria Island vacation rentals with private pools, perfect for relaxing getaways with family, friends, or pets. From Anna Maria to Holmes Beach, Bradenton Beach, & right Off Island, our homes offer privacy, comfort, and easy access to the island’s best beaches, shops, and restaurants.

Our local team is here to ensure a seamless stay, offering personalized support and insider tips to make your vacation unforgettable. Whether you’re bringing your pup  or planning a family retreat, you’ll find the ideal home for your island escape.

Properties Available 42 properties available
Welcome to Point's Hideaway!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Please note: The home is next to a construction site. There is no set construction schedule, and activity may occur during your stay.The SpaceEvery corner of Point’s H
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Point's Hideaway
Point's Hideaway
Anna Maria Pet Friendly
$340.00 - $990.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.7 (8)
Welcome to Sunset at 714!On Anna Maria Island (Anna Maria, FL)Managed locally by Once Upon A Beach Vacation Rentals & Property ManagementThe SpaceWhere island sunsets, beach days, and family memories come together.Tucked away on the highly desirable north end of Anna Maria Island, Sunset at 714 places you just a short stroll from the sugar-whit
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Sunset at 714
Sunset at 714
Anna Maria
$410.00 - $1,900.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (1)
Welcome to Island Girl West!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit: Island Girl West*Step inside Island Girl West, where natural textures, sunlight, and soft coastal hues set the tone for your stay. The open layout invites easy flow between kitchen, dining, and living spaces
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Island Girl West
Island Girl West
Holmes Beach
$230.00 - $620.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (4)
Welcome to Anna Maria Aloha!On Anna Maria Island (Anna Maria, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience Anna Maria Aloha — a tranquil island cottage made for rest, renewal, and connection.Nestled on the peaceful North End of Anna Maria Island, just 500 feet f
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Anna Maria Aloha
Anna Maria Aloha
Anna Maria Pet Friendly
$270.00 - $790.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (13)
Welcome to Sea La Vie Beach House!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceWhere connection meets calm, Sea La Vie Beach House brings family, friends, and loved ones together in a space designed for comfort, laughter, and easy island liv
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Sea La Vie Beach House
Sea La Vie Beach House
Anna Maria
$560.00 - $2,400.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (11)
Welcome to Family Tides – Unit A!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit; Family Tides A (Bottom Unit)*Located just steps from the Gulf of Mexico and walkable to Bridge Street, this ground-level unit invites you to unwind, connect, and enjoy a thoughtfully
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Family Tides - A
Family Tides - A
Bradenton Beach
$42.00 - $980.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Welcome to Sunsets on Carissa!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.The SpaceEvery corner of this home is designed to bring people together. The open-concept layout connects the kitchen, dining, and living areas, so laughter and conversation flow as
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Sunsets on Carissa
Sunsets on Carissa
Holmes Beach
$330.00 - $847.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (14)
Welcome to Sol Mate!On Anna Maria Island (Anna Maria, FL)Managed locally by Once Upon A Beach Vacation Rentals & Property ManagementThe SpaceYour island escape designed for families and friends to slow down, reconnect, and soak in the simple joys of island life. Nestled near Anna Maria’s most scenic shoreline and moments from Pine Avenue,
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Sol Mate
Sol Mate
Anna Maria Pet Friendly
$390.00 - $1,010.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (13)
Welcome to Island Girl East!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit: Island Girl East*Discover Island Girl East, a bright coastal retreat just five houses from the beach. Here, mornings begin with the sound of swaying palms, and afternoons drift between the pool and the sea.
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Island Girl East
Island Girl East
Holmes Beach
$230.00 - $620.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4 (3)
Welcome to Kokomo!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceDiscover Kokomo, where comfort meets calm in a thoughtfully updated beach cottage just a short walk from the Gulf of Mexico. Designed for rest and reconnection, this home
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Kokomo
Kokomo
Holmes Beach
$250.00 - $748.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (11)
Welcome to Hidden Palms!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agencyThe SpaceTucked into a quiet Holmes Beach neighborhood, this elevated island retreat invites you to slow down and settle into the rhythm of island life. Sunlight fills the home from above,
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Hidden Palms
Hidden Palms
Holmes Beach
$300.00 - $825.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Welcome to Mango Bay!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Set on a quiet street near the sand, Mango Bay blends open interiors with plenty of outdoor living. Upstairs, the main living floor brings kitchen, dining, and lounge spaces together
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Mango Bay
Mango Bay
Holmes Beach
$370.00 - $940.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.6 (5)

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When is the best time to visit Anna Maria Island?

Anna Maria Island is beautiful any time of year, but different seasons are best for different activities. Spring and fall both have warm temperatures and fewer crowds, and are perfect for a more relaxed vacation spent enjoying the outdoors and checking out local attractions. Summer is the hottest and busiest time of year. If you’re looking for exciting summer energy, summer is your best bet. Winter in Anna Maria Island has cooler temperatures and the lowest prices.

Are dogs allowed on the beaches in Anna Maria Island?

Most of the beaches on Anna Maria Island do not allow dogs, so it’s important to check the regulations before bringing your pup. But even if you can’t bring your four-legged family member to one of the main beaches, there are plenty of alternatives, like Palma Sola Causeway Park & Bayfront Park. View Pet Friendly Rentals in Anna Maria Island.

What are the best beaches on Anna Maria Island?

Every beach on the island is fantastic! We love Bean Point, on the northern tip of the island, for its views, wildlife viewing, and spectacular shelling. Bradenton Beach is great for anyone looking for a mix of relaxation and activities, with easy access to biking trails and restaurants. And Holmes Beach is lovely for anyone who wants to swim in clear waters or relax in the sugar-soft sands the island is famous for. Rentals within walking distance to the beach

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